D-(+)-Glucuronic acid γ-lactone

• CAS: 32449-92-6
• Catalog Number: ACM32449926
• Category: Main Products
• Molecular Weight: 176.12
• Molecular Formula: C₆H₈O₆
• Synonyms: dicurone; 6-lactone; D-glucuronic acid-3-lactone; D-(+)-Glucurono-3,6-lactone; guronsan; glucuronolactone; D-(+)-Glucuronic acid γ-lactone; glucurone; D-Glucuronsaeure-3-lacton; glucuron; glycurone; reulatts.s.; Glucuronolactone; D-Glucurone; D(+)-Glucurono-3,6-lactone; D-(+)-Glucurono-6,3-lactone; D-Glucurono-6,3-lactone; Glucoxyl; D-glucuronolactone; glucoxy; D-Glucuronic Acid Lactone
• IUPAC Name: D-glucurono-6,3-lactone
• Boiling Point: 403.5ºC at 760 mmHg
• Melting Point: 170-176ºC
• Flash Point: 174.9ºC
• Density: 1.749 g/cm³
• Appearance: white crystalline powder
• Exact Mass: 176.03200
• Hazard Statements: Xi: Irritant
• Safety Description: S24/25
• Stability: Stable under normal temperatures and pressures.
• WGK Germany: 2

Case Study

Glucuronic Acid γ-Lactone as a Piezoelectric Organic Crystal for Sensor Applications

Saripalli, Ravi Kiran, et al. Applied Physics A 122.4 (2016): 438.

Glucuronic acid γ-lactone (glucuronolactone) is an organic compound that crystallizes in a polar space group. Large single crystals (1.2 × 1.0 × 0.6 cm³) grown from aqueous solution by slow cooling exhibit piezoelectric resonance, making the material promising for electromechanical sensing.
Experimental Protocol: Crystals were grown from saturated solution cooled from 38 °C to 28 °C at 0.05 °C/h. Powder XRD was refined by the Rietveld method. UV-Vis transmission of a (010) plate (2 mm thick) was measured from 200-900 nm. Dielectric response was recorded at 1 kHz-10 MHz from 80-300 K on silver-electroded plates. Piezoelectric coefficients were calculated from resonance/antiresonance frequencies.
Performance Evaluation: XRD confirmed lattice parameters a = 6.616 Å, b = 6.758 Å, c = 7.486 Å, β = 93.308°. The UV cutoff was 250 nm; the optical band gap was 4.96 eV (indirect transition). Piezoelectric resonance peaks appeared at 0.1-1.5 MHz, shifting to lower frequencies with increasing temperature and broadening with temperature rise. At room temperature, the electromechanical coupling coefficient k₃₁ was 0.589, elastic compliance S₁₁ = 4.27 × 10^-11 N^-1 m², and piezoelectric coefficient d₃₁ = 19.3 × 10^-12 C N^-1, comparable to some inorganic piezoelectrics.
Conclusion: Glucuronic acid γ-lactone is a wide-bandgap organic piezoelectric material with potential for resonant sensors and electro-optic devices.

Glucuronic Acid γ-Lactone as an Organic Nonlinear Optical Crystal with High Laser Damage Threshold

Saripalli, Ravi Kiran, et al. Optical Engineering 56.1 (2017): 011025-011025.

Glucuronic acid γ-lactone (glucuronolactone) is an organic nonlinear optical (NLO) crystal that exhibits high second-harmonic generation (SHG) efficiency and exceptionally high laser-induced damage threshold (LIDT), making it suitable for high-power laser applications.
Experimental Protocol: Single crystals were grown from aqueous solution by slow cooling. SHG efficiency was measured by the Kurtz-Perry powder method using a Q-switched Nd:YAG laser (1064 nm, 10 ns, 10 Hz). LIDT was determined on (010) plates with 6-ns pulses at 1064 nm and 5-ns pulses at 532 nm. Thermal properties were analyzed by TGA/DSC/DTA.
Performance Evaluation: The SHG efficiency was 3.5 times that of KDP. Conic rings from spontaneous noncollinear phase matching indicated type II phase matchability and high birefringence. Surface LIDT values at 1064 nm were 77.72 ± 0.27 GW/cm² (single shot) and 32.72 ± 0.41 GW/cm² (multiple shot, 3000 pulses). At 532 nm, values were 25.23 ± 0.33 and 9.87 ± 0.25 GW/cm², respectively. TGA/DSC showed a melting point of 171 °C and a specific heat of 1.24 J/g·°C at 30 °C. Damage morphology revealed local melting, decomposition, and cleavage along (101) and (001) planes.
Conclusion: Glucuronic acid γ-lactone is a promising organic NLO material with high SHG efficiency, high laser damage threshold, and good thermal stability, suitable for frequency conversion in high-power laser systems.

D-Glucuronolactone as a Hepatoprotective Agent Against Thioacetamide-Induced Liver Fibrosis

Chen, Po-Ju, et al. Journal of Functional Foods 14 (2015): 154-162.

D-Glucuronolactone, a naturally occurring metabolite of glucose, exhibits hepatoprotective effects by reducing oxidative stress, inflammation, and fibrosis in thioacetamide (TAA)-treated rats.
Experimental Protocol: Male Wistar rats received intraperitoneal TAA (100 mg/kg) three times weekly for 8 weeks, with or without daily oral D-glucuronolactone (75 mg/kg). Serum liver enzymes (AST, ALT), hepatic antioxidant markers (SOD, GPx, GSH, TEAC, TBARS), inflammatory/fibrotic gene expression (NF-κB, AP-1, KLF-6, IL-6, α-SMA, COLα1), and histopathology were assessed.
Performance Evaluation: D-Glucuronolactone significantly lowered elevated AST (p < 0.05) but not ALT. It increased antioxidant capacity: SOD and GPx activities, GSH and TEAC levels (p < 0.05), while decreasing TBARS. Gene expression of NF-κB, AP-1, KLF-6, IL-6, α-SMA, and COLα1 was down-regulated (p < 0.05). Histopathology showed reduced inflammatory cell infiltration and collagen accumulation (Masson's trichrome) compared to TAA-only controls. The compound also ameliorated TAA-induced body weight loss and organ enlargement.
Conclusion: D-Glucuronolactone attenuates TAA-induced liver fibrosis by enhancing antioxidant defenses and suppressing inflammatory/fibrotic pathways, supporting its use as a functional ingredient for liver protection.

D-Glucuronolactone as a Hepatic Lipid-Lowering Additive via the Enterohepatic Axis in Laying Hens

Shen, Yiru, et al. Journal of Animal Science and Biotechnology 17.1 (2026): 38.

D-Glucuronolactone (D-Glu) reduces hepatic lipid accumulation and improves laying performance in hens by remodeling hepatic lipid profiles, downregulating fatty acid synthesis genes, and modulating gut microbiota.
Experimental Protocol: LMH avian hepatocytes were treated with palmitic acid (400 µmol/L) or tert-butyl hydroperoxide (tBHP) to induce lipid accumulation and oxidative stress, followed by D-Glu (100 µmol/L). In vivo, 42-week-old Hy-Line brown laying hens received dietary D-Glu (280 mg/kg) for 12 weeks. Liver lipidomics, cecal microbiota (16S rRNA), egg yolk fatty acids (GC-MS), and gene expression (qRT-PCR) were analyzed.
Performance Evaluation: D-Glu reduced intracellular triglyceride (TG) and lipid droplet area in LMH cells (p < 0.05), and decreased reactive oxygen species levels. In hens, D-Glu increased laying rate and egg mass, lowered liver TG and fatty liver scores (p = 0.049), and reduced abdominal fat width (p = 0.002). Lipidomics revealed decreased hepatic TG and diglyceride species, particularly those containing C18:1 and C18:2 fatty acids, while phospholipids increased. Gene expression of FASN, ACSL, PPAR-γ, CD36, and FABP1 was downregulated (p < 0.05). Cecal abundance of Bacteroides, CHKC1001, and Angelakisella increased, and Firmicutes/Bacteroidetes ratio decreased. Egg yolk polyunsaturated fatty acids (e.g., linoleic, arachidonic) were elevated.
Conclusion: D-Glucuronolactone alleviates hepatic steatosis and improves egg nutritional quality via the enterohepatic axis, offering a nutritional strategy for fatty liver syndrome in laying hens.

Synthetic Use

Upstream Synthesis Route 1

• 2671-19-4

• 32449-92-6

Reference: [1] Chemische Berichte, 1933, vol. 66, p. 1326,1328
[2] Journal of the American Chemical Society, 1952, vol. 74, p. 4377

Upstream Synthesis Route 2

• 6556-12-3
• 100-39-0

• 32449-92-6

Reference: [1] Tetrahedron, 2007, vol. 63, # 32, p. 7596 - 7605

Upstream Synthesis Route 3

• 6556-12-3

• 32449-92-6

Reference: [1]Recueil des Travaux Chimiques des Pays-Bas,1952,vol. 71,p. 999,1003

Upstream Synthesis Route 4

• 87-89-8

• 32449-92-6

Reference: [1]Journal of the American Chemical Society,1958,vol. 80,p. 2022

Downstream Synthesis Route 1

• 32449-92-6

• 15384-34-6

Reference: [1] Canadian Journal of Chemistry, 1956, vol. 34, p. 693,699

* For details of the synthesis route, please refer to the original source to ensure accuracy.